2-(2-Fluorophenyl)ethylamine → HCID 11749646, compound

HRID 422231Notes

Reaction equation

HRID 422231 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][CH2:29][NH2:30].[BH3-]C#N.[Na+]>Cl[Ti](Cl)(Cl)Cl>[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][CH2:29][NH:30][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6433572-(2-Fluorophenyl)ethylamineHCID 5003444Sodium cyanoborohydrideHCID 597506396-(1-Oxo-indan-5-yloxy)-nicotinamide2×

Product 1

HCID 11749646HCID 11749646, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

Using a method similar to Example 1, using 6-(1-oxo-indan-5-yloxy)-nicotinamide (Intermediate 4, 805 mg, 3.00 mmol), 2-(2-fluorophenyl)ethylamine (501 mg, 3.60 mmol), Ti(iPrO)4 (1.70 g, 6.00 mmol), TiCl4 (1.0M/DCM, 6.00 ml, 6.00 mmol), and NaBH3CN (377 mg, 6.00 mmol) gives the title compound (398 mg) as a white solid. Mass spectrum (ion spray): m/z=392 (M+1); 1HNMR (CDCl3): 8.58 (s, 1H), 8.15 (d, 1H), 7.32 (d, 1H), 7.25-7.17 (m, 2H), 7.09-7.00 (m, 2H), 6.98 (s, 1H), 6.94 (d, 2H), 5.93 (br. s, 2H), 4.28 (t, 1H), 3.04-2.95 (m, 3H), 2.92-2.87 (m, 2H), 2.83 (ma, 1H), 2.45 (m, 1H), 1.85 (m, 1H).

Sources & evidence

ORD record
ord-e4746f706d5e45249fc754439224a0aa
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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